Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers
Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbe...
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Veröffentlicht in: | Journal of organic chemistry 2024-06, Vol.89 (11), p.7630-7643 |
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creator | Liu, Yuheng Yuan, Lutong Dai, Linlong Zhu, Qiaohong Zhong, Guofu Zeng, Xiaofei |
description | Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. NHC desymmetrization produces axially chiral diaryl ether atropisomers with high yields and enantioselectivities in moderate circumstances. Chiral diaryl ether compounds may be precursors for highly functionalized diaryl ethers with bioactivity and chiral ligands for asymmetric catalysis. |
doi_str_mv | 10.1021/acs.joc.4c00330 |
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Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. NHC desymmetrization produces axially chiral diaryl ether atropisomers with high yields and enantioselectivities in moderate circumstances. Chiral diaryl ether compounds may be precursors for highly functionalized diaryl ethers with bioactivity and chiral ligands for asymmetric catalysis.</description><identifier>ISSN: 0022-3263</identifier><identifier>ISSN: 1520-6904</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.4c00330</identifier><identifier>PMID: 38738853</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>bioactive properties ; carbenes ; catalytic activity ; chemotypes ; esterification ; heterocyclic nitrogen compounds ; ligands ; organic chemistry ; stereoselective synthesis</subject><ispartof>Journal of organic chemistry, 2024-06, Vol.89 (11), p.7630-7643</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a320t-520cab53b3acc17ae775eab5d24b551c61855446bb7668fd61c26f49408af4e23</cites><orcidid>0000-0001-9497-9069 ; 0000-0003-4222-1365</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.4c00330$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.4c00330$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38738853$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Yuheng</creatorcontrib><creatorcontrib>Yuan, Lutong</creatorcontrib><creatorcontrib>Dai, Linlong</creatorcontrib><creatorcontrib>Zhu, Qiaohong</creatorcontrib><creatorcontrib>Zhong, Guofu</creatorcontrib><creatorcontrib>Zeng, Xiaofei</creatorcontrib><title>Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. NHC desymmetrization produces axially chiral diaryl ether atropisomers with high yields and enantioselectivities in moderate circumstances. Chiral diaryl ether compounds may be precursors for highly functionalized diaryl ethers with bioactivity and chiral ligands for asymmetric catalysis.</description><subject>bioactive properties</subject><subject>carbenes</subject><subject>catalytic activity</subject><subject>chemotypes</subject><subject>esterification</subject><subject>heterocyclic nitrogen compounds</subject><subject>ligands</subject><subject>organic chemistry</subject><subject>stereoselective synthesis</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkM9LwzAUx4Mobk7P3qRHQbrld7vj6DYVBl70HJL0lXV0zUxaYf71Rjq9ibk8Ej7vm_c-CN0SPCWYkpm2YbpzdsotxozhMzQmguJUzjE_R2OMKU0ZlWyErkLY4XiEEJdoxPKM5blgY7QutDfQQlroTjfHTyiTRefdwQVowHb1BySFa0Pn-3hxbeKqpNjWXjfJstb-2CSrbgs-XKOLSjcBbk51gt7Wq9fiKd28PD4Xi02qGcVdGmez2ghmmLaWZBqyTEB8KCk3QhArSS4E59KYTMq8KiWxVFZ8znGuKw6UTdD9kHvw7r2H0Kl9HSw0jW7B9UExIpikhAjyP4rjT4zEuSI6G1DrXQgeKnXw9T6upwhW355V9KyiZ3XyHDvuTuG92UP5y_-IjcDDAAydvW-jlj_jvgBAvoeD</recordid><startdate>20240607</startdate><enddate>20240607</enddate><creator>Liu, Yuheng</creator><creator>Yuan, Lutong</creator><creator>Dai, Linlong</creator><creator>Zhu, Qiaohong</creator><creator>Zhong, Guofu</creator><creator>Zeng, Xiaofei</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0001-9497-9069</orcidid><orcidid>https://orcid.org/0000-0003-4222-1365</orcidid></search><sort><creationdate>20240607</creationdate><title>Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers</title><author>Liu, Yuheng ; Yuan, Lutong ; Dai, Linlong ; Zhu, Qiaohong ; Zhong, Guofu ; Zeng, Xiaofei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a320t-520cab53b3acc17ae775eab5d24b551c61855446bb7668fd61c26f49408af4e23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>bioactive properties</topic><topic>carbenes</topic><topic>catalytic activity</topic><topic>chemotypes</topic><topic>esterification</topic><topic>heterocyclic nitrogen compounds</topic><topic>ligands</topic><topic>organic chemistry</topic><topic>stereoselective synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Yuheng</creatorcontrib><creatorcontrib>Yuan, Lutong</creatorcontrib><creatorcontrib>Dai, Linlong</creatorcontrib><creatorcontrib>Zhu, Qiaohong</creatorcontrib><creatorcontrib>Zhong, Guofu</creatorcontrib><creatorcontrib>Zeng, Xiaofei</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Yuheng</au><au>Yuan, Lutong</au><au>Dai, Linlong</au><au>Zhu, Qiaohong</au><au>Zhong, Guofu</au><au>Zeng, Xiaofei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2024-06-07</date><risdate>2024</risdate><volume>89</volume><issue>11</issue><spage>7630</spage><epage>7643</epage><pages>7630-7643</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. NHC desymmetrization produces axially chiral diaryl ether atropisomers with high yields and enantioselectivities in moderate circumstances. Chiral diaryl ether compounds may be precursors for highly functionalized diaryl ethers with bioactivity and chiral ligands for asymmetric catalysis.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38738853</pmid><doi>10.1021/acs.joc.4c00330</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0001-9497-9069</orcidid><orcidid>https://orcid.org/0000-0003-4222-1365</orcidid></addata></record> |
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subjects | bioactive properties carbenes catalytic activity chemotypes esterification heterocyclic nitrogen compounds ligands organic chemistry stereoselective synthesis |
title | Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers |
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